


A Tale of Two Organizations

by darkdisrepair



Category: Chicago PD (TV)
Genre: Agent Hailey Upton, Alternative Universe - FBI, Enemies to Friends to Lovers, F/M, Hailey is a sassy bean, also a style icon
Language: English
Status: In-Progress
Published: 2020-06-09
Updated: 2020-06-11
Packaged: 2021-03-03 20:34:31
Rating: Teen And Up Audiences
Warnings: Creator Chose Not To Use Archive Warnings
Chapters: 4
Words: 4,295
Publisher: archiveofourown.org
Story URL: https://archiveofourown.org/works/24631630
Author URL: https://archiveofourown.org/users/darkdisrepair/pseuds/darkdisrepair
Summary: Intelligence clashes with an FBI unit that comes to Chicago. Their casual camaraderie contrasts with the no-nonsense approach that the FBI takes, and Jay in particular clashes with the unit's Agent In Charge, Hailey Upton.But there's something between, something that he can't quite put his finger on. It might take him months, or even years, but he figures it out.
Relationships: Jay Halstead/Hailey Upton
Comments: 16
Kudos: 68





	1. Chapter 1

**Author's Note:**

> the first two chapters were originally posted on tumblr, but i liked this idea, so here we go! updates probably won't be EVERY DAY but we'll see how motivated I get ;) some edits were made to add detail.

“Are you serious? Just like that?” Jay demanded, following Voight into his office. “We’ve been tracking this trafficking ring for weeks, and you’re going to let the Feds get their paws all over it?”

Voight let out a breath.

“They have jurisdiction over us.”

“That’s bullshit.”

“That’s how it works. I’m sorry, Halstead, I’m just as frustrated as you over this. But at least they’re working with us.”

Jay rolled his eyes. “Yeah, right.”

* * *

The first day with the Feds was a mess. Everyone kept talking over each other and none of the files were organized, so they got almost nothing done, which was infuriating to no end. He spent a long time trying to keep the agents from messing up their whiteboard, which they seemed to have a disdain for, which made him like them even less than he'd liked them the first time he met them. 

They were wasting time.

Jay made eye contact with one of the agents- a small blonde, who stood in the back, staring at the situation without saying anything. She held his gaze for a long, tense moment before clearing her throat.

“Here’s what we’re going to do. We’re going to split into groups. CPD in one and FBI in the other. We’re going to compile our evidence in a civilized manner and we’re going to present them to each other, like grown-ups,” she said, and the other agents fell silent. Jay raised his eyebrows- this agent seemed to have more control over the room than he'd anticipated. She just seemed like a random agent from the unit, but now he wasn't so sure. “Are you all capable of that?”

Jay snorted. “No offense, agent, but we’re not schoolchildren. This isn’t a group project. This is a drug trafficking ring we’re talking about.”

The blonde agent stepped forward, blue eyes blazing. “I don’t see any adults in this room, do you, _detective?_ Someone has to play teacher or no one will learn anything.”

With that, she turned on her heel. “Agents, you’re with me.”

In that moment, Jay decided that he hated her. Whatever her name was. 

* * *

The next day, Jay came into the bullpen at the normal time, to find that the lights were already on and someone was working in there. 

That someone being a slight, petite blonde in a blazer.

Definitely not one of the members of Intelligence.

“How’d you get up here?” 

Agent Ponytail jumped, spinning around in her chair- his chair, rather. “Your desk sergeant buzzed me up," she said, tilting her head to the side, which made him feel almost as if _he_ were the one out of bounds.

“What, the presentations yesterday not enough for you? Did we score too low for your standards?” 

Deep down, Jay knew he was being an ass, but he didn’t care. There was something about her that got under his skin.

“Those presentations only scratched the surface. I’m organizing my team’s evidence and looking for yours for things that we missed,” she answered, eyebrows raised. “We needed to get something done yesterday, and we did. But it’s not enough.”

“Then why did we waste our time?”

“It wasn’t a waste of time. We already had a few breakthroughs, if you remember- which comes from looking at evidence in a different way. Believe it or not, I know what I’m doing.”

Jay blinked. He didn’t know what to say to that. 

“Well, next time you come up here, be out of my desk by 7:15,” he said finally, before walking away.

* * *

On a raid the next day, an FBI agent blew his cover by forgetting to take off his wedding ring.

The case went downhill after that.

Jay heard the shots over the radio, but by the time he got there, the firefight was over, and three agents, one officer, and two offenders were dead.

* * *

After that, it was like someone lit a fire behind the blonde agent’s- Hailey Upton, he learned- eyes. 

There was no one else who stayed longer or arrived earlier than she did. She ran her unit with an iron tight fist after the first mistake, double checking and triple checking every file, every wire, every word that they ever said or saw. 

Despite his intense disdain for her and her unit, he felt bad- it couldn’t have been easy to have lost three agents under her command. They walked around the district with tired eyes and wore all black a week- their own version of funeral rites, Jay guessed. So almost two weeks later, after catching her half-asleep at his desk at midnight, he brought her coffee that morning.

Just once.

She approached Jay the next day, tugging him into the locker room without warning, which almost made him spill his coffee. Lucky for her, he didn't, otherwise he suspected she would have needed a trip to the drycleaner. 

“I need you for an undercover op,” she said without preamble.

He agreed, even though he didn’t fancy listening to her directions all the time.

* * *

The first thing she said to Jay when they saw Holden, the second in command of the ring was _we need to leave._

“I’m not about to let him go,” he hissed, yanking her forward. “We’re six bodies in, in case you haven’t noticed.”

“We’re walking into a trap.”

“You can’t possibly know that,” he said, before following Holden into the run down old house across the street.

She didn’t follow.

* * *

“Ah, well if it isn’t little Intelligence boy,” Holden sneered, brandishing his gun when Jay rounded the corner.

And instantly, he knew he’d made a mistake. 

He heard three pops.

The first sent him sprawling on his back, pain jolting through his body from the form of the bullet.

The next two ripped holes in Holden’s chest, one just above his heart, the next, dead center.

And then he saw her. She looked almost angelic, with her bright eyes and blonde hair as she fumbled with his jacket.

“Why’d you follow me?” he managed, as he tried to catch his breath.

She didn’t answer for a long time, just checked his vest methodically, with an almost impersonal detachment. When she found no blood, she sat back on her heels and let out a sigh. “I care about you,” she said finally. “And I hate how much I care about you. Backup is backup, whether I agree with you or not.”

“Next time, do me a favor and take someone with you. Because I’m not going to be in Chicago every time you run off by yourself.”


	2. Chapter 2

**Summary for the Chapter:**

> hailey returns to chicago for the second time.

"Detective Halstead!”

Jay halted in his tracks, just a few steps from entering the 21st District. The voice sounded familiar, but he couldn’t place who it was. Not until he turned around to see Agent Hailey Upton standing at the bottom of the stairs, dressed impeccably in a dark blue blazer, not that he should have expected otherwise.

“Agent Upton,” he said, leaning against the railing. “New York’s a long way from here.”

“We caught a case,” she answered, stepping closer so that they didn’t have to yell between the various patrolmen who kept coming out of the doors. “And as it turns out, we need your help.”

“Hold on a minute, back up there. What did you just say?”

She glared daggers at him. “I won’t repeat myself again. You heard me the first time.”

“Excuse me for basking in this glorious moment. It’s not often the FBI admits that they need help from the police. The fact that it’s coming from _your_ mouth makes it all the more of a profound moment.”

“I can always go to another district,” she said, eyebrows raised.

“Do you have academy training before becoming an FBI agent? Because you clearly missed out on the humor classes. I’ve met doors that laughed more than you do.”

“I’ve chased drug dealers with better aim than yours. I guess that means we’re even.”

“So, what’s this case?” Jay asked, as she brushed past him. 

“Oh, wouldn’t you like to know?” she said, giving him a sideways smirk before disappearing inside the District. 

* * *

Hours later found both of the teams scouring a football arena for signs of a bomb, which was infuriating because the FBI agents kept getting in the way.

“Scratch what I said before, the class you missed was definitely how to properly search a building,” Jay grumbled when he nearly ran into Upton for the third time. “They’re not going to put a bomb here.”

“And you clearly don’t understand that criminals are unpredictable. No class is going to teach you this. Then again, if you cops figured out how to catch criminals, I’d be out of a job.”

Jay watched her walk over to the bathroom wall. “A soap dispenser, really? A bomb’s not going to fit there.”

Upton pulled down the plastic and stepped back to reveal a mess of C4 and wires nestled within the dispenser. “Point proven. I’m liking our team-up more and more, detective. It’s becoming quite the hobby of mine to prove you wrong.”

* * *

After successfully defusing the bomb, both teams gathered in the bullpen for a celebratory drink. 

By now, the agents and the Intelligence unit were starting to bond, just a little. He spotted Kim and Kevin playing desk ping pong with two other agents, and Vanessa attempting some sort of demented game of tic-tac-toe with another.

Upton leaned up against Jay’s desk, surveying it all without saying anything, and despite himself, Jay found himself walking over. 

“Staying out of the fun, Agent?” he asked, quirking an eyebrow at her.

“This isn’t ‘fun’. This is waiting for the inevitable storm.”

“Well, aren’t you just Miss Cheerful.” 

As he said 'Miss', he found himself searching for a ring on her left hand- but all he found an ink stain, which he knew had happened when she signed the incident report from the day. He couldn't tell if he was disappointed, or relieved that she wasn't married.

“I’m Greek, I look for tragedy, not comedy, in everything,” she said, without taking her eyes off the other members of her unit. “It was too easy. We chased this guy halfway across the country to find a bomb in a soap dispenser. It just doesn’t sit right with me. Not in the slightest.”

“Cases are just like that sometimes. Complex at first, then simple. It’s okay to celebrate,” he told her. “Let loose a little.”

Why was he trying to comfort her? They weren’t friends. Not in the slightest. But he hated to see the tired slump to her shoulders, hated how subdued she was despite the major victory they’d just accomplished.

“Yeah, right,” she snorted, just as her phone buzzed in her pocket. She pulled it out, paling noticeably at the name that appeared on the screen. “Agent Upton. Yes. Yes. No, I haven’t looked at the news.”

Never a good sign.

Her eyes flickered over to Jay in the silence that followed. “Yes. I’ll get them together. Thank you.”

With that, she hung up. “A senator was just murdered in New York,” she said. She didn’t even sound surprised. “Guess the party will have to wait.”

“I guess so.”

“Enjoy the fun. I’m sure our paths will cross again. Let’s hope that by then, you’ve brushed up on your ‘searching for bombs’ education.”

With that, she pushed herself off of his desk and started walking to the stairs. Immediately, the babble and chatter ceased, as all of the members of her unit automatically stopped what they were doing. “Agents, celebration’s over. Duty calls.”


	3. Chapter 3

**Summary for the Chapter:**

> once again, the fbi agents are back. this time, without a certain blonde.

The next time that the FBI came, almost six months later, Jay didn't find out until he nearly ran into someone wearing an FBI jacket at the top of the stairs. More specifically, a certain smiley, tall, muscular agent. 

"Agent Atwater," he said.

"Always the tone of surprise with you," Atwater answered. "It's nice to see you again, man."

The agent extended his hand for a handshake, which Jay took, unconsciously glancing around the bullpen for the other members of the unit. Sure enough, there was the other ponytailed agent- Agent Bell, who waved at him- and the other tall, brooding agent- Agent Zidan- along with another partnership, who Jay hadn't ever really talk to. "Likewise," he said absently.

"Agent Upton is on undercover assignment with Agent Garrett."

Jay blinked. "What?"

"You were looking for her. She left five months ago, haven't heard a word from her since," Atwater said. "I was going to tell you, but I wasn't sure if it would be appropriate. We don't work together that much in reality. I didn't want to overstep."

"I'm not her boyfriend, I don't need to know what she's doing or what she's not doing with her time. I'm just glad to see you, it's been a while. How's the unit? What case are you here for?"

"We're investigating a terrorist threat, per usual. We're about to wrap it up, we just wanted to stop by and say hi to everyone. Our unit's grown kind of fond of you guys."

As he said it, Atwater's eyes drifted toward a certain officer- a smaller officer, with braids. Vanessa. 

Jay raised his eyebrows. "Of course."

"I'm glad we could catch you before we left," Atwater continued. "We always try to catch the Chicago cases before they get passed on to other units. We missed a few but I think Agent Bell is putting in a request to Agent Castile to see if it can be a more permanent partnership."

"Ah."

"Voight's on board, if that's what you're wondering about."

"I was more wondering if Agent Upton is on board. She seems to have a very intense dislike for Chicago, and this unit."

Atwater raised his eyebrows. "She wouldn't sass you if she didn't like you, and she, more than anyone, would not come back to this city if she wasn't okay with working with your unit."

"What-"

"I'll try and contact you when she's out of undercover. It might be a while."

* * *

Jay had a hard time concentrating for the rest of the day. 

Why did Agent Atwater assume that he wanted to know about Agent Upton? They weren't friends. Not even close. They weren't enemies, exactly, but her disdain for him and the Chicago police department was pretty obvious.

Or was it?

Had he just misread her character completely? 

He wasn't going to lie- he enjoyed the quick banter between the two of them- but there was always a little bit more weight to her comments than the ribbing he got form the other FBI agents. For her, it was more personal. 

"Whatcha thinking about?" Vanessa asked, scooting over to his desk in her chair. 

"What? Nothing."

"Doesn't look like nothing. You're doing that forehead crinkle thing, and your eyes are all starry. Thinking about someone?" the younger officer prodded, a wide grin on her face. 

"I'm not," Jay protested.

"You definitely are. Is it a certain feisty blonde, perhaps? You miss her, don't you?"

"I do not miss her. She's just an FBI agent, Vanessa, I barely know her. I have no reason at all to miss her. I don't know why everyone keeps asking me about her. She's the most irritating out of all of them."

"Mhmm."

"I really don't need your sass right now."

"You just can't handle the heat, but okay, I'll stop bothering you," Vanessa said, and scooted away again, spinning in her chair as she went. 

Jay rolled his eyes. 

Rookies.

* * *

The FBI's last visit to Chicago seemed to have ignited a spark between the two groups. A week after the agents left, Jay was added to a new groupchat between all of the members of Atwater's unit and the members of Intelligence. After that, it didn't take long for someone to start sharing memes instead of information. The agents were a little more reserved than the officers, but Jay quickly adjusted to their dark humor, and found himself laughing at his phone at odd hours of the night.

There was a noticeable hitch in the camaraderie, which bothered Jay. He couldn't quite place what was off until he was scrolling through the contacts list within the group chat and spotted an unfamiliar icon.

'HAILEY UPTON'.

And then everything clicked into place. The FBI agents's humor was off because they kept subconsciously waiting for her to jump in and complete the joke, or fill in the gaps of a story, which never happened because she wasn't there to do it. 

While Intelligence came off as a well-oiled machine in the chat, the FBI unit was fractured, limping along without the blonde agent to complete the set.

And just like that, Jay understood why everyone was so fixated on her from the FBI perspective. She did more than everyone thought. When the groups started clashing, she was the one to mediate, which she usually did while throwing in a few gibes in for good measure. She was the one to crack a joke when things got too heavy, and usually the one to pull together two different strands of evidence and connect them.

In that sense, Jay missed her.

But that was it.

He might have been the one to clash with her most, but by the way that Atwater and Zidan kept bringing her up, they were the ones who suffered from her absence the most. Atwater was her partner, and Zidan- Jay wasn't sure. Boyfriend wasn't likely, but there was something there- a certain fondness.

Slowly, as the months crawled by, Upton's name appeared less and less in the thread. There wasn't really a reason to talk about her when she wasn't there. It was clear that the agents still missed her, desperately, but they kept their melancholy to themselves. 

They tried to hide it, but Jay could tell they were getting nervous about her undercover placement. He couldn't figure out if it was just because it was undercover, which was always emotionally draining, or if it was because her case was escalating. 

Either way, he didn't envy them. 

Worrying about an agent or officer undercover was not fun.

Undercover was like a whole new world. There was no such thing as friends, unless you went under with a partner. There was a lot of looking over shoulders and paranoia and threats and shady happenings, deals in the dark, promises that might or not have to be kept. 

Jay didn't wish that stress on anyone. Not even Agent Hailey Upton.


	4. Chapter 4

**Summary for the Chapter:**

> hailey's undercover case takes her to chicago.

"Got any mail for me, Sergeant Platt?" Jay asked, leaning up against the desk. 

"Just a few things. Some subpoenas, some reports that didn't go through..." Platt said as she flipped through his stack. "Here you go."

"Sergeant Platt!"

A familiar authoritative voice cut through the usual clamor of the District, and Jay turned to see Commander Perry stride through the doors. "Is Voight around?"

"Upstairs. Detective Halstead can buzz you up," Platt said. Jay nodded. 

"Follow me."

He led the Commander up the stairs, feeling more than a little awkward as he scanned his palm under the reader. Perry didn't necessarily seem agitated, which was rare when he was dealing with Voight, but sometimes it was impossible to tell. 

"Relax, Detective, the sky's not gonna fall," Perry said.

"Who said it was?"

Once they reached the top of the stairs Perry immediately beelined toward Voight's office. Only then did Jay notice the thick folder in his hand. 

The two exchanged a few words before emerging from the office, one after the other. Voight came around to the whiteboard, standing with his hands in his pockets, looking unshaken. "We have a new case that Commander Perry has brought to my attention. A meth ring has moved into Chicago, led by a notorious dealer known as Ronald Booth."

"Why bring this to us?" Jay asked, unable to stop himself. "There's a lot of meth rings in Chicago."

"This one's different. Ronald Booth is one of the best in the business in terms of dealing. Taking him down would take down a nationwide network of seasoned dealers and scare a few of them out in the process. Not only that, but his meth is more potent than most. Ever since he came into town a month or two, we've seen a noted increase in overdoses."

Perry pulled a few photos out of his file. "This is Booth," he said, sticking a picture of a salt-and-pepper haired man in the center of the board. "Know his face- because you'll be chasing him for weeks. And these are a few of his associates that we've been able to pinpoint. Scott Jansen is one of his low-level dealers. We also suspect Booth's nephew of being in the game- he works with Booth."

"There are two other members of the ring we haven't been able to identify as easily. The first being this man," Perry continued, pulling out a blurry photo of a dark, bearded guy in dark jacket. "We think he's closer to the top of Booth's business, along with this woman."

Another photo- this one of a blonde with smooth hair, almost like it was straightened. "They're always just out of sight of cameras, but we have intel that they're usually around Booth's warehouse, too. They're newer to the crowd, according to information from some other police departments. Almost no one can pinpoint who they are."

"So what's our play?" Vanessa asked. "Sounds like these guys know what they're doing."

"We'll find one of them to flip. I'm thinking either Jansen or the nephew," Perry said.

Voight immediately shook his head. "Absolutely not. The nephew is too close. And Jansen won't mean anything to this case. It's easy to catch him in it, and flipping him means nothing if we can't connect him to something solid. He won't have any of the big product on him."

"So what do you recommend?"

Voight tilted his head, considering the board. "The two unknowns. You said they're pretty new. That means they'll be looking to win Booth's favor, but they might not have it yet. The loyalty won't be there. Are they a package deal?"

"Showed up at the same time, according to NYPD."

"Alright. Then we'll arrest them both, see if we can get them to come the good side," Jay said. "Easy."

* * *

It wasn't easy. 

The blonde girl and dark haired guy were like ghosts. Impossible to pin down, no matter how hard the unit tried. They tried tailing them in cars, on foot- but it was like they knew someone was watching.

Either they were legit professionals, or just really paranoid.

After nearly a week, Perry returned, a little less friendly the first time. "Look, Voight, we tried it your way. Jumping the line didn't work. If we don't get them in handcuffs by the end of the week, we're going for Jansen, understand?"

"Copy that."

Once the Commander left, Voight turned to the rest of the unit. "Here's what you're going to do. You're going to find out where they've been staying and you're going to camp out there, out of sight, until you can catch them unawares. We've got enough evidence to call for their arrest, all you have to do is stay out of sight until you get the opportunity."

* * *

After three hours of intense research, the team split up to three different apartment building locations. Jay covered the front stairwell while Kim went to the back, and one of the patrolmen watched the street.

"Blonde coming your way," Jay heard in his earpiece.

As soon as Jay heard the door open, he grabbed for the figure in the doorway, pulling the blonde by the arm and pinning her against the wall, gun pressed between her shoulderblades. "Chicago PD, move and I shoot."

"What the hell?!" the blonde exclaimed. "What is this?"

"You're under arrest for the distribution of illegal substances."

"You gotta let me go," she said.

There was something familiar about her voice, but Jay didn't place it until after he'd wrestled handcuffs onto her wrists and turned her around to come face-to-face with Agent Hailey Upton.

"Ag-"

"Not here."

* * *

As soon as they got in the car, Upton turned around. "You have to let me go," she said. 

"I can't do that," Jay said, although now he wasn't so sure. "I'm under orders from the Commander of the CPD. You're gonna have to take up with Voight. I'm sorry."

"Fucking police officers," Upton grumbled. "You just couldn't stay away, could you?"

"You're the one who's running a meth ring in Chicago, I don't think you can say much," Jay retorted, as they pulled into the district. "Just be glad we're the ones on the case and not someone else."

"Be glad that you're going to blow my cover? I don't think so."

"We're not going to blow your cover."

"Oh, yeah? Then why are you dragging me all the way across the city to a police station? Seems like the least productive way to maintain someone's undercover identity... or did you miss that class in the Academy, too?"

"I could have outed you right then and there. Be glad I arrested you and _didn't_ let you go. Where's your partner?"

"Oh, no, no, no, you're not about to burn both of us. Call off your unit."

"I can't do that, either. I'm not in charge. Voight is."

"Then let me talk to Voight."

"You really don't want to do that, sweetheart."

Upton gave him a glare capable of murder. "Don't you ever call me that, or you'll have more problems than just working for a shitty organization- you'll have an angry FBI agent to deal with, too."

"I'm terrified," Jay said amusedly.

"You should be."


End file.
